Nonlinear optical properties of some derivatives of salicylaldimine-based ligands

Karakas, A.; Elmalı, Ayhan; Ünver, Hüseyin; Svoboda, Ingrid

doi:10.1016/j.molstruc.2004.06.017

Cited by 86 publications

(37 citation statements)

References 26 publications

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“…It has been previously reported that the phenolic carbon atom of imines is more shielded than the corresponding carbonyl carbon atom of enamines (δ ≈ 160 ppm vs. δ ≈ 180 ppm). [41] A similar trend can be inferred from 15 N NMR spectroscopy, since the imine nitrogen atom is much more shielded than that atom in the enamine tautomer (δ ≈ -63 ppm vs. δ ≈ -247 ppm). [42,[44][45][46][47][48] In the present case, the carbon resonance at δ ≈ 165 ppm for compounds 20 and 21 can be attributed to C-2 in a phenol-imine structure, whereas 22 shows a signal at δ ≈ 180 ppm, consistent with a keto-enamine structure.…”

Section: Structures In Solutionsupporting

confidence: 56%

Schiff Bases from TRIS and ortho‐Hydroxyarenecarbaldehydes: Structures and Tautomeric Equilibria in the Solid State and in Solution

Martínez¹,

Авалос²,

Babiano³

et al. 2011

Eur J Org Chem

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Three Schiff bases generated by conventional condensation of a simple aminopolyol (TRIS) and 5‐bromo‐ and 5‐iodosalicylaldehyde, and 2‐hydroxy‐1‐naphthaldehyde, have been fully characterized, both in solution and in the solid state. This study provides a complete analysis of imine–enamine equilibria, and sheds light onto the mechanism of hydrogen transfer, which has been controversial in the literature. Low‐temperature X‐ray diffraction accompanied by electron‐density maps have further been complemented by theoretical studies at the B3LYP/6‐31G* and M06‐2X/6‐311++G** levels. To ascertain the influence of crystal packing on tautomeric stability, the lattice has also been simulated by computation. This protocol involves the assessment of a supramolecular cluster around a core tautomer possessing either imine or enamine structures. Such an analysis, in full agreement with solid‐state data, reveals the greater stability of zwitterionic structures for the salicyl derivatives. In contrast, these substances show preferential imine forms in solution, whereas the naphthyl‐based compound exhibits a prevalent keto‐enamine structure in all cases.

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Section: Structures In Solutionsupporting

confidence: 56%

Schiff Bases from TRIS and ortho‐Hydroxyarenecarbaldehydes: Structures and Tautomeric Equilibria in the Solid State and in Solution

Martínez¹,

Авалос²,

Babiano³

et al. 2011

Eur J Org Chem

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show abstract

“…The computational approach allows to determine molecular NLO properties in an inexpensive way. The microscopic nonlinear response in organic molecules, especially ab-initio MP2 calculations, allow a relatively accurate prediction of the NLO activity [11,12]. The Schiff base system studied here has donor a hydroxy (-OH) group at ortho positions and two acceptor chloro (-Cl) substituents at ortho and para positions.…”

Section: Computational Results and Discussionmentioning

confidence: 99%

Study On The Second Order Optical Properties Of N-(2,4-Dichloro)-Salicylaldimine

Karakas

Ünver

Elmalı

et al. 2005

Zeitschrift Für Naturforschung A

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N-(2,4-Dichloro)-salicylaldimine was synthesized, characterized by elemental analysis, FT-IR, and UV-visible spectroscopy, and its crystal structure was determined. The title compound is almost planar and contains short intramolecular O-H. . . N hydrogen bonds [O1-N1 2.601(1)Å]. It remains transparent in the visible region and has solvatochromic behavior in the UV region in the range 198 -349 nm, implying non-zero microscopic first hyperpolarizability. The ab-initio quantum mechanical calculations (finite field second-order Møller Plesset perturbation theory) of the studied compound have been carried out to compute the electric dipole moment (µ µ µ) and the first hyperpolarizability (β β β ) values. The ab-initio results also show that this ligand might have microscopic nonlinear optical behavior with non-zero values.

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“…[13,14] There are several research works on Schiff bases because it is a promising material for NLO applications. In this series, Karakas et al [15] reported the first order hyperpolarizability of salicylaldimine based ligands using computational calculations. The second harmonic generation (SHG) and electric field induced second harmonic generation (EFSHG) studies were discussed together with the theoretically calculated first order hyperpolarizability for a series of organotin(IV) Schiff-base complexes by Rivera et al [16] The third order NLO property of 3-hydroxyquinoxaline-2-carboxalidine-4-aminoantipyrine Schiff base was studied by Arun et al [17] experimentally by using z-scan technique.…”

Section: Introductionmentioning

confidence: 99%

Role of charge transfer on the nonlinear optical properties of donor-π-acceptor (D-π-a) conjugated schiffbases with DFT approach

Vijayalakshmi

Kalyanaraman²

2016

J. Phys. Org. Chem.

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D-π-A conjugated systems of two Schiff bases have been investigated using density functional theory method. Experimental observations on charge transfer (CT) using ultraviolet-visible absorption study have been verified by time-dependent density functional theory calculations. The transition corresponding to CT absorption band is found to be HOMO 0 → LUMO 0 . The HOMO-LUMO picture along with the natural bond orbital analysis show the highly delocalized CT interaction in the ring system, and it could be attributed to the large value of first order hyperpolarizability (β) at molecular level. However, owing to the lack of effective CT in the D-π-A system at molecular level, there is no effective second harmonic generation observed at solid state. But in the case of third order nonlinear optical property, the presence of strongest donor in a molecule causes the large value of second order hyperpolarizability (γ).

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Nonlinear optical properties of some derivatives of salicylaldimine-based ligands

Cited by 86 publications

References 26 publications

Schiff Bases from TRIS and ortho‐Hydroxyarenecarbaldehydes: Structures and Tautomeric Equilibria in the Solid State and in Solution

Schiff Bases from TRIS and ortho‐Hydroxyarenecarbaldehydes: Structures and Tautomeric Equilibria in the Solid State and in Solution

Study On The Second Order Optical Properties Of N-(2,4-Dichloro)-Salicylaldimine

Role of charge transfer on the nonlinear optical properties of donor-π-acceptor (D-π-a) conjugated schiffbases with DFT approach

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